The Greatest Celebrity Gamblers of All Time

Gambling has become something of a pop culture phenomenon. It has featured in dozens of movies, TV shows, and music videos, usually as a means of connoting a devil-may-care attitude and a luxurious lifestyle. It is – above all – a status symbol, a way to show off the mega-money of the rich and famous.   

But, off-screen, there are lots of stars who enjoy having a flutter in real life too, from A-list actors through to music moguls. For example, whilst we’re all familiar with the starring turn of Matt Damon in Rounders, outside of acting, it’s his best friend Ben Affleck who’s a poker supremo, and, whilst Elvis might have crooned about Las Vegas, it’s his Rat Pack counterpart Frank Sinatra who really set the city alight.    

So, without further ado, here are some of the greatest celebrity gamblers ever to have lived. 

Ben Affleck 

Ben Affleck is an exceptionally talented actor but off-set, his life is no less exciting, and much of it is spent in casinos across the US. Whilst he might have money to burn, this doesn’t mean he’s frivolous: Affleck is actually a hugely gifted poker player who frequently profits from his gaming. Besides the two Oscars that he can lay claim to, the father of three has enjoyed an awful lot of success behind the tables, reaching semi-professional status. He’s not only played in numerous tournaments but even claimed victory in one Californian championship back in 2004. If we weren’t convinced of it already, we’d be marvelling at how he has more skill in his little finger than the rest of us do in our entire bodies.      

Frank Sinatra

The Rat Pack was an informal group of entertainers who lit up the Las Vegas casino scene. Frank Sinatra was at the heart of the Vegas scene, so it’s no surprise to learn that he held an appreciation for both the bright lights of big city living and  the joys of gambling. Frequenting the casinos even before he became a celebrity, Sinatra enjoyed everything from poker to baccarat to blackjack.  We bet he’d have loved the way modern tech has made it possible to play these popular games without even having to leave our homes – indeed, without even having to open our laptops! The only difference when he became famous was that he was able to wager even more often and more impressively than he had done pre-riches.   

50 Cent 

50 Cent is known to have an appreciation for all forms of gambling but his true love is said to be sports betting. He famously wagered an astonishing $1.6 million on Floyd Mayweather Jr when he went up against Manny Pacquiao in a boxing match – and came out of it victorious. Although no one is quite sure how much his winnings amounted to, with the star having remained tight-lipped and secretive regarding the sum, one can only presume that it was an arguably impressive amount. The rapper, actor and TV producer is also a huge fan of the New York Giants and is reported to have placed some pretty dramatic bets on them in the past, though it’s assumed that none have been quite as large as his most famous flutter. 

Honestly, who wouldn’t want these lucky celebrities’ lives for themselves? Oh, to be a fly on the wall in the casinos where they play!

Written by Monella